Magnesium → HCID 86720839, compound

HRID 1482172Notes

Reaction equation

HRID 1482172 reaction equation
[Mg].Br[C:3]1[CH:14]=[CH:13][C:12]2=[C:15]3[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]3[C:9]([CH3:21])([CH3:20])[C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=12>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:21][C:9]1([CH3:20])[C:8]2[C:15]3[C:4]([CH:5]=[CH:6][CH:7]=2)=[C:3]([C:3]2[CH:14]=[CH:13][C:12]4=[C:15]5[C:4]=2[CH:5]=[CH:6][CH:7]=[C:8]5[C:9]([CH3:20])([CH3:21])[C:10]2[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=24)[CH:14]=[CH:13][C:12]=3[C:11]2[CH:16]=[CH:17][CH:18]=[CH:19][C:10]1=2

Participants

5

Reactant 2

HCID 5462224MagnesiumHCID 68229424HCID 68229424, compound

Product 1

HCID 86720839HCID 86720839, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

After addition of magnesium powder (659 mg, 27.1 mmol) to 200 mL of THF in a nitrogen atmosphere, the mixture was refluxed at the boiling point and thereafter a solution of the 3-bromo-7,7-dimethylbenzo[a]phenalene (17.5 g, 54.2 mmol) in 800 mL of THF was added dropwise and the mixture was stirred for 1 hour. Then, tetrakis(triphenylphosphine)palladium (624 mg, 0.542 mmol) was added to the reaction solution and the mixture was refluxed at the boiling point for 2 hours to obtain 3-(7,7-dimethylbenzo[a]phenalen-3-yl)7,7-dimethylbenzo[a]phenalene at a yield of 56%. The 3-(7,7-dimethylbenzo[a]phenalen-3-yl)7,7-dimethylbenzo[a]phenalene (3.00 g, 6.16 mmol) and anhydrous aluminum chloride (4.11 g, 30.8 mmol) were dispersed in 400 mL of chlorobenzene and the dispersion was heated to 80° C. and stirred for 5 hours to synthesize Illustrative Compound A-4 at a yield of 33%.

Workup

  1. temperaturethe mixture was refluxed at the boiling point
  2. temperaturethe mixture was refluxed at the boiling point for 2 hours

Sources & evidence

ORD record
ord-b1e378c723084c4f8f6d05fa17341172
Source dataset
uspto-grants-2016_08
Patent number
US09412952B2

Reaction notes

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